Halogen-magnesium exchange reaction of iodoindoles with ethylmagnesium bromide in THF undergoes smoothly to give indolylmagnesium bromides which react with various electrophiles.Halogen-lithium exchange reaction has been extensively studied for the preparation of aromatic and heteroammatic lithium compounds.'Lithioindoles have been prepared using halogen-lithium exchange reaction of haloindoles, however preparation of 3-IithioN-phenylsulfonylindole from the 3-icdoindole derivative can be 2 done under strictly controlled reaction conditions (-100°C), and at higher temperature, the 3-lithioindole are.known to isomerize to the corresponding Zlithioindole.The isomerization is avoidable only when a bulky group such as ten-butyldimethylsilyl group was introduced as a protecting group of indole.3Oxidative addition reaction of metallic magnesium to haloaromatics and haloheteroaromatics has been widely used
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Sakamoto et al. (1996) studied this question.